ChemFOnt: Showing chemical card for Nicain (CFc000333275)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:12 UTC

Chemfont ID

CFc000333275

Molecule Identification

Common Name

Nicain

Definition

Nicotinic acid, also known as niacin or 3-pyridinecarboxylic acid, is a member of the class of compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Nicotinic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Nicotinic acid can be found in a number of food items such as grapefruit, lemon grass, nopal, and loquat, which makes nicotinic acid a potential biomarker for the consumption of these food products. Nicotinic acid can be found primarily in most biofluids, including blood, feces, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Nicotinic acid exists in all living species, ranging from bacteria to humans. In humans, nicotinic acid is involved in the nicotinate and nicotinamide metabolism. Moreover, nicotinic acid is found to be associated with alcoholism. Nicotinic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Nicotinic acid is a drug which is used for the treatment of type iv and v hyperlipidemia. it is indicated as ajunctive therapy. Niacin cannot be directly converted to nicotinamide, but both compounds are precursors of the coenzymes nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP) in vivo. NAD converts to NADP by phosphorylation in the presence of the enzyme NAD+ kinase. NADP and NAD are coenzymes for many dehydrogenases, participating in many hydrogen transfer processes. NAD is important in catabolism of fat, carbohydrate, protein, and alcohol, as well as cell signaling and DNA repair, and NADP mostly in anabolism reactions such as fatty acid and cholesterol synthesis. High energy requirements (brain) or high turnover rate (gut, skin) organs are usually the most susceptible to their deficiency . Nicotinic acid can cause vasodilation of cutaneous blood vessels resulting in increased blood flow, principally in the face, neck and chest. This produces the niacin- or nicotinic acid-flush. The niacin-flush is thought to be mediated via the prostaglandin prostacyclin. Histamine may also play a role in the niacin-flush. Flushing is the adverse reaction first observed after intake of a large dose of nicotinic acid, and the most bothersome one. LD₅₀ 7000 mg/kg (Rat) (DrugBank). Nicotinic acid can cause vasodilation of cutaneous blood vessels resulting in increased blood flow, principally in the face, neck and chest. This produces the niacin- or nicotinic acid-flush. The niacin-flush is thought to be mediated via the prostaglandin prostacyclin. Histamine may also play a role in the niacin-flush. Flushing is the adverse reaction first observed after intake of a large dose of nicotinic acid, and the most bothersome one (T3DB).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Carboxypyridine	ChEBI
3-Pyridinecarboxylic acid	ChEBI
3-Pyridylcarboxylic acid	ChEBI
Acide nicotinique	ChEBI
Acido nicotinico	ChEBI
Acidum nicotinicum	ChEBI
Anti-pellagra vitamin	ChEBI
beta-Pyridinecarboxylic acid	ChEBI
m-Pyridinecarboxylic acid	ChEBI
Niacin	ChEBI
Nikotinsaeure	ChEBI
P.P. factor	ChEBI
Pellagra preventive factor	ChEBI
PP Factor	ChEBI
Pyridine-beta-carboxylic acid	ChEBI
Vitamin b3	ChEBI
Niacor	Kegg
Niaspan	Kegg
3-Pyridinecarboxylate	Generator
3-Pyridylcarboxylate	Generator
b-Pyridinecarboxylate	Generator
b-Pyridinecarboxylic acid	Generator
beta-Pyridinecarboxylate	Generator
Β-pyridinecarboxylate	Generator
Β-pyridinecarboxylic acid	Generator
m-Pyridinecarboxylate	Generator
Pyridine-b-carboxylate	Generator
Pyridine-b-carboxylic acid	Generator
Pyridine-beta-carboxylate	Generator
Pyridine-β-carboxylate	Generator
Pyridine-β-carboxylic acid	Generator
Nicotinate	Generator
3-Carboxylpyridine	HMDB
Akotin	HMDB
Apelagrin	HMDB
Daskil	HMDB
Efacin	HMDB
Enduracin	HMDB
Linic	HMDB
Niac	HMDB
Niacine	HMDB
Nicacid	HMDB
Nicamin	HMDB
Nicangin	HMDB
Nico-span	HMDB
Nicobid	HMDB
Nicocap	HMDB
Nicodelmine	HMDB
Nicolar	HMDB
Niconacid	HMDB
Nicosan 3	HMDB
Nicotinipca	HMDB
Nicyl	HMDB
Nyclin	HMDB
Pellagrin	HMDB
Pelonin	HMDB
Slo-niacin	HMDB
Wampocap	HMDB
Aluminum salt, niacin	HMDB
Induracin	HMDB
Niacin cobalt (2+) salt	HMDB
Niacin iron (2+) salt	HMDB
Niacin lithium salt	HMDB
Niacin magnesium salt	HMDB
Niacin sodium salt	HMDB
Nico-400	HMDB
Potassium salt, niacin	HMDB
Sodium salt, niacin	HMDB
Tosylate, niacin	HMDB
Nicotinate, lithium	HMDB
Hydrochloride, niacin	HMDB
Niacin aluminum salt	HMDB
Niacin calcium salt	HMDB
Niacin copper (2+) salt	HMDB
Niacin hydrochloride	HMDB
Niacin lithium salt, hemihydrate	HMDB
Nico400	HMDB
Tartrate, niacin	HMDB
3 Pyridinecarboxylic acid	HMDB
Lithium nicotinate	HMDB
Niacin ammonium salt	HMDB
Niacin manganese (2+) salt	HMDB
Niacin potassium salt	HMDB
Niacin tartrate	HMDB
Niacin tosylate	HMDB
Niacin zinc salt	HMDB
Nico 400	HMDB

Chemical Formula

C₆H₅NO₂

Average Molecular Weight

123.1094

Monoisotopic Molecular Weight

123.032028409

IUPAC Name

pyridine-3-carboxylic acid

Traditional Name

niacin

CAS Registry Number

59-67-6

SMILES

OC(=O)C1=CN=CC=C1

InChI Identifier

InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)

InChI Key

PVNIIMVLHYAWGP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents

Substituents

Pyridine carboxylic acid
Heteroaromatic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridine alkaloid (CHEBI:15940 )
pyridinemonocarboxylic acid (CHEBI:15940 )
Water-soluble vitamins (C00253 )
Pyridine alkaloids (C00253 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0001488)

Food

Nut

Cashew nut (FooDB: FOOD00011)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	83.1 g/L	ALOGPS
logP	0.29	ALOGPS
logP	-0.17	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	4.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.19 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	31.16 m³·mol⁻¹	ChemAxon
Polarizability	11.3 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon